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WO2008020983A2 - Colorant capillaire d'oxydation par l'air catalysée - Google Patents

Colorant capillaire d'oxydation par l'air catalysée Download PDF

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Publication number
WO2008020983A2
WO2008020983A2 PCT/US2007/016980 US2007016980W WO2008020983A2 WO 2008020983 A2 WO2008020983 A2 WO 2008020983A2 US 2007016980 W US2007016980 W US 2007016980W WO 2008020983 A2 WO2008020983 A2 WO 2008020983A2
Authority
WO
WIPO (PCT)
Prior art keywords
air oxidation
water soluble
content
oxidation haircolor
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2007/016980
Other languages
English (en)
Other versions
WO2008020983A3 (fr
Inventor
Jack Massoni
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Combe Inc
Original Assignee
Combe Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to EP07810885.9A priority Critical patent/EP2059306B1/fr
Priority to JP2009523771A priority patent/JP5339374B2/ja
Priority to MX2009001485A priority patent/MX2009001485A/es
Priority to NZ574744A priority patent/NZ574744A/en
Priority to BRPI0716024A priority patent/BRPI0716024B1/pt
Priority to CN200780029613.6A priority patent/CN101528310B/zh
Priority to HK09108629.3A priority patent/HK1128897B/en
Priority to ES07810885.9T priority patent/ES2537083T3/es
Priority to AU2007284979A priority patent/AU2007284979B2/en
Priority to CA2659998A priority patent/CA2659998C/fr
Application filed by Combe Inc filed Critical Combe Inc
Priority to US12/310,084 priority patent/US7758659B2/en
Publication of WO2008020983A2 publication Critical patent/WO2008020983A2/fr
Publication of WO2008020983A3 publication Critical patent/WO2008020983A3/fr
Anticipated expiration legal-status Critical
Priority to US12/658,457 priority patent/US7947090B2/en
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55—Phosphorus compounds

Definitions

  • Oxidation hair dyes are normally sold in the form of a two- component kit.
  • an alkaline composition that contains oxidation dyes and an appropriate vehicle.
  • a developer composition that utilizes an oxidizing agent, usually hydrogen peroxide.
  • the two compositions are mixed immediately prior to use and applied to the hair.
  • the alkaline pH of the mixture causes the hair shaft to swell, allowing the dye precursors to penetrate into the cortex of the hair. These dye precursors are then oxidized, which combine to form larger molecules.
  • U.S. patent 4,004,877 uses metal salts complexed with tartaric acid in an air oxidation system. The resulting colors on hair are still very light with a single application. Additionally, the composition requires the use of formamide as solvent. For safety reasons, this material is no longer acceptable for use in cosmetic products.
  • U.S. patent 6,648,925 takes this technology a step further by capturing the metal catalyst within a clathrate or zeolite compound in an air oxidation composition. These are inclusion complexes where the metal ions are completely enclosed within the crystal structure of another compound. These are difficult formulations to prepare, and are not practical for commercial application.
  • the object of this invention is to provide formulations and manufacturing methods that achieve the level of color deposition, and wear properties equivalent to two part "deposit only oxidation haircolorants", but from a single component air oxidation product.
  • These formulations use known dye intermediates and other cosmetic ingredients in unique combinations which produce an unexpected degree of gray coverage. Additionally, due to the absence of an oxidizing agent other than atmospheric oxygen, the compositions are milder, less damaging to the hair, and have better color retention than traditional two part systems.
  • the invention includes a specific catalyzed air oxidation haircolor composition that will provide a significant increase in gray coverage over existing technology, while maintaining safety, good wear properties, and ease of use.
  • the consistency of the formulas may be modified to produce a gel or slightly viscous lotion suitable for dispensing from an aerosol container.
  • the compositions provided by this invention are susceptible to premature air oxidation, and must therefore be prepared and stored under anaerobic conditions.
  • the composition should contain the following ingredients: 1. 70 - 95% water 2. 0.1 - 1.0% of a water soluble metal salt
  • an organic solvent system such as one consisting of a combination of isopropanol and isopropyl acetate, or ethanol and ethyl acetate.
  • the vehicle used to carry the dye intermediates allows for very high levels of water in the finished formulas.
  • the water can range from 70 - 95% of the composition. Lighter shades using fewer dyes will be at the higher end of the range, while dark brown and black shades will be closer to the 70% level.
  • This high level of water creates a very efficient carrier for the dye systems, which normally would not deposit on gray hair to the level that is present for the formulas covered by this invention.
  • the formulas need to catalyze the oxidation process within the hair structure.
  • the preferred catalysts are water soluble metal salts include copper, cobalt, zinc, silver, nickel and iron salts, preferably with non-toxic anions such as the sulfate, chloride, nitrate, carbonate, phosphate or organic acid salts such as the fumarate, citrate, tartrate and the like.
  • Water soluble manganese salts are preferred because they create the most color deposition when added to the formulas at levels of 0.1 - 1.0%. More preferably, the concentration of the anhydrous salt should 0.3 - 0.7%, based on the total weight of the salt in the composition.
  • Dye take on gray hair will drop off on either side of the above mentioned ranges.
  • the most preferred anions to be used in conjunction with manganese are sulfate or chloride, although nitrates, carbonates, phosphates, fluoride, or bromide are acceptable.
  • Additional color enhancement on gray hair can be achieved by the addition of a specific chelating agent called etidronic acid or also known as l-hydroxyethane-1,1- diphosphonic acid.
  • etidronic acid or also known as l-hydroxyethane-1,1- diphosphonic acid.
  • the structure is indicated below.
  • the chelating affect with the manganese ions helps limit the amount of manganese that remains within the hair structure after the compositions are removed by rinsing and shampooing. Some metal ions such as copper or iron, will leave the hair feeling rough and damaged. Manganese's affect on hair is not as dramatic as the more common transition metals, but it is still prudent to limit the amount remaining in the hair after a color treatment.
  • the amount of etidronic acid required works well from 0.03 — 0.3% when used with the prescribed level of manganese salt. Below this range the color saturation drops off, and above the 0.3% level long term stability is compromised and color delivery is also negatively impacted.
  • the air oxidation colorants discussed in this invention use conventional oxidation dye primary intermediates.
  • the most useful of these include: p-Phenylenediam ⁇ ie, N,N- Bis(2-Hydroxyethyl)-p-Phenylenediamine Sulfate, p-Aminophenol, and p- Toluenediamine.
  • Others can include: 2-Chloro-p-Phenylenediamine, N-Phenyl-p- Phenylenediamine, p-Methylaminophenol, 1 - Amino-4-(2-Methoxyethyl)-aminobenzene, 2,4,5,6-Tetraaminopyrimidine, 2-(Hydroxymethyl)-p-Phenylenediamine, 3-Methyl-p- Aminophenol, 2-(2-Hydroxyethyl)-p-Phenylenediamine, 4,4'-Diaminodiphenylamine, 1,3- Dimethyl-2,5 -Diaminobenzene, 2-isopropyl-p-Phenylenediamine, N-(beta- hydroxypropyl)-p-Phenylenediamine, 2-Methyl-p-Aminophenol, 2-Propyl-p-
  • Phenylenediamine 2-(2'-Hydroxyethylaminomethyl)-p-Aminophenol, 2-
  • the invention includes the use of aromatic triols such as 1 ,2,4-benzenetriol, 1,3, 5- triethylhydroxybenzene, tris(2-hydroxyethyl)isocyanurate and the like as the useful dye couplers in all compositions.
  • aromatic triols such as 1 ,2,4-benzenetriol, 1,3, 5- triethylhydroxybenzene, tris(2-hydroxyethyl)isocyanurate and the like
  • the preferred coupler is 1,2,4-benzenetriol This material will combine with the primary intermediates in the preceding paragraph to form the oxidation condensate which is trapped within the hair structure. These compounds produce the majority of the brown coloration for the formulas derived from this technology.
  • the dye concentration should vary from 0.1 % to 3% depending upon the final depth of color desired.
  • the formulas may be modified by the addition of other dye couplers.
  • the most useful of these include: Resorcinol, 4-Chlororesorcinol, 2-Methylresorcinol, m- Aminophenol, 1-Naphthol, 1,5-Naphthalenediol, 2,7-Napthalenediol, 2,4-Diaminophenol, Hydroxybenzomorpholine, l-Hydroxy-3-Dimethylaminobenzene, 4-Amino-2-
  • antioxidants or reducing agents should be used to maximize the shelf life of the finished product.
  • a typical two part oxidation haircolor system will use up to 1% of antioxidants to ensure stability during manufacture and in the final package. This level is too high in order to achieve the highest level of color deposition on the hair.
  • the range to be used in this invention should be 0.1 - 0.3% of the total formula. Below this level will result in poor long term stability, and above the designated range will result in poor color deposition.
  • the most appropriate reducing agents may include: sodium sulfite, bisulfite salts, thioglycolate salts, erthorbic acid, ascorbic acid, thiosulfate salts, and other related materials.
  • surfactants are required in the formulas in order to quickly wet out the hair, produce lather, and allow for ease of rinsing.
  • concentration should be restricted to 1 - 5 % of the total formula. By keeping to this range, the products maintain their high water content and the resulting efficiency in delivering color to the hair.
  • surfactants can be any cosmetically acceptable anionic, amphoteric, or nonionic material that will produce sufficient lather. These can be as simple as Alkyl sulfates, Alkyl ether sulfates, or fatty acid soaps. More preferably the surfactants should produce a milder affect on the skin, as the working pH of the formulas is between 9 and 10. These can include: Amphoacetates, Alkyl polyglycosides, Amphodiacetaes,
  • Amphohydroxypropylsulfonates Amphopropionates, Amidopropyl Betaines, Sultaines, Alkylamidopropylamine Oxides, Alkylamine Oxides, Alkanolamides, Sulfocuccinates, and related compounds.
  • the formulas should be thickened with water soluble anionic polymers referred to as Carbomer.
  • Carbomer water soluble anionic polymers
  • carbomers which are manufactured by the Noveon Corporation under the Carbopol name.
  • carbomers can be described as high molecular weight homo and copolymers of acrylic acid cross linked with a polyalkenyl polyether having a viscosity, as measured in water, at 0.5- 1.0% w/v of about 3,000-60,000 mPa s.
  • Examples of these include: Carbopol Ultrez 10, Carbopol 940, Carbopol 941, Carbopol 980, Carbopol ETD 2050, Carbopol 981, Carbopol 934, Carbopol 2984, and Carbopol 5984. Similar materials are produced by other manufacturers and can go by the CTFA designation of carbomer. These materials should be used in the formulations at 0.5 — 2.0% to produce a moderately viscous liquid to a gel form. A water soluble solvent system is used to assist in dye solubility and help in carrying the dye intermediates to the hair's cortex.
  • solvents are contained within the aromatic triol or in particular , the benzentriol premix, and are a result of the reaction from benzenetriacetate to the triol form. Either isopropanol or ethanol can be used as a medium to carry out this reaction.
  • the resulting solution will contain the aromatic triol such as the 1,2,4-Trihydroxybenzene, plus the alcohol, plus the corresponding acetate compound (either ethyl acetate or isopropyl acetate) depending on the particular aromatic triol.
  • the final formulation will contain 0.5 — 10% of these solvent systems depending upon the level of the aromatic triol such as benzenetriol that is a required for the particular shade.
  • the best color deposition for the formulas contained within this invention occurs from pH 9 - 10.
  • a quantity sufficient of a cosmetically acceptable alkalizer to achieve this pH is required.
  • the alkalizer can either be organic or inorganic in nature. These can include ethanolamine, triethanolamine, aminomethyl propanol, ammonium hydroxide, carbonates, bicarbonates, and other similar materials.
  • Experimental Procedures and Results The following is a list of various shades that can be produced by using the technology discussed in this invention. The shade descriptor is matched on 90% bended gray hair as dyed out in the laboratory, and on clients as listed in Table ⁇ . In all instances the development time was 10 minutes, followed by rinsing, shampooing, and blow drying.
  • Level 2 Dark Brown/Black
  • Level l Black
  • the water content of the formulas for these air oxidation colorants has a significant impact on the amount of color deposition within hair and other keratin fibers.
  • a minimum water content of 70% is required in order to maximize the color take.
  • Example 6 was dyed out for 10 minutes on 90% gray hair and compared to the control Medium Brown shade used in example 3.
  • the swatch appearance for example 6 was more like a shade in between dark blonde and light brown. L.a.b readings confirm this observation.
  • the pH of the compositions requires a restriction of pH 9 to pH 10.
  • Formulations on either side of this range show lighter color deposition than the control Medium Brown shade of example 3.
  • This formula has a pH of 9.3.
  • Examples 7, 8, and 9 were prepared at pH 6.9, 8.8, and 10.3; respectively. Even the products that are close to the desired range show some indication of lighter color deposition than the control. All formulas were dyed out for 10 minutes on 90% gray hair and compared to the control Medium Brown shade used in example 3. L.a.b. readings are illustrated in the chart below.
  • the manganese salt concentration performs best in regards to color delivery on hair when used at a level of 0.1 — 1.0%.
  • the control formula of the Medium Brown shade shown in example 3 contains 0.5% manganese sulfate.
  • Examples 10, 11 and 12 uses 0.05%, 0% and 2% manganese sulfate respectively.
  • These compositions that are just outside the range of the invention indicate lower color deposition as illustrated by the dyeouts and color measurements taken in the chart below. All formulas were dyed out for 10 minutes on 90% gray hair and compared to the control Medium Brown shade used in example 3. L.a.b. readings were taken for each swatch.
  • the Etidronic Acid used within the context of this invention works best at concentrations of 0.03 — 0.300. At the upper limits, the color deposition on hair is starting to diminish but is still useful.
  • the control Medium Brown shade uses 0.03% etidronic acid. Examples 13 and 14 use 0.3% and 0% etidronic acid respectively. All formulas were dyed out for 10 minutes on 90% gray hair and compared to the control Medium Brown shade used in example 3. L.a.b readings are illustrated in the chart below.
  • Example 16 A typical formula to convert benzenetriacetate to benzenetriol would be shown in example 16. However, the amounts can vary significantly, and is only limited by the solubility of the triol. Example 16 would yield a solution of about 10% benzenetriol.
  • composition is applied to hair without mixing with an oxidizing agent, and left on the hair for 5 — 15 minutes, rinsed and shampooed.
  • melts are by weight based on the total weight of all components of the composition.
  • moderately viscous means a viscosity of 500 — 5000 cps as determined by a Brookfield Viscometer, model number DV-E, using spindle T-C at 6 rpm at a temperature of 23° C.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
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  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne une composition de colorant capillaire d'oxydation par l'air à base: a) d'eau ; b) de sel métallique soluble dans l'eau comme catalyseur ; c) d'acide étidronique (acide l-hydroxyéthane-l,l-diphosphonique) comme agent chélatant et agent augmentant le dépôt de la couleur ; d) d'intermédiaires de colorant primaire d'oxydation ; e) d'un triol aromatique tel que le l,2,4-benzènetriol ; f) de coupleurs de colorant d'oxydation auxiliaire ; g) d'anti-oxydants et de stabilisants de colorant ; h) facultativement d'un agent tensioactif soluble dans l'eau ; i) facultativement d'un polymère anionique soluble dans l'eau ; j) d'un système solvant soluble dans l'eau ; et k) un alcalinisant.
PCT/US2007/016980 2006-08-10 2007-07-30 Colorant capillaire d'oxydation par l'air catalysée Ceased WO2008020983A2 (fr)

Priority Applications (12)

Application Number Priority Date Filing Date Title
AU2007284979A AU2007284979B2 (en) 2006-08-10 2007-07-30 A catalyzed air oxidation haircolor
MX2009001485A MX2009001485A (es) 2006-08-10 2007-07-30 Tintura para el cabello de oxidacion al aire catalizada.
NZ574744A NZ574744A (en) 2006-08-10 2007-07-30 A catalyzed air oxidation haircolor
BRPI0716024A BRPI0716024B1 (pt) 2006-08-10 2007-07-30 corante capilar de oxidação catalisada em contato com o ar.
CN200780029613.6A CN101528310B (zh) 2006-08-10 2007-07-30 催化的空气氧化染发剂
HK09108629.3A HK1128897B (en) 2006-08-10 2007-07-30 A catalyzed air oxidation haircolor
ES07810885.9T ES2537083T3 (es) 2006-08-10 2007-07-30 Tinte capilar de oxidación por aire catalizada
EP07810885.9A EP2059306B1 (fr) 2006-08-10 2007-07-30 Colorant capillaire d'oxydation par l'air catalysée
JP2009523771A JP5339374B2 (ja) 2006-08-10 2007-07-30 触媒空気酸化ヘアカラー
CA2659998A CA2659998C (fr) 2006-08-10 2007-07-30 Colorant capillaire d'oxydation par l'air catalysee
US12/310,084 US7758659B2 (en) 2006-08-10 2007-07-30 Catalyzed air oxidation haircolor
US12/658,457 US7947090B2 (en) 2006-08-10 2010-02-04 Catalyzed air oxidation haircolor

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US83687606P 2006-08-10 2006-08-10
US60/836,876 2006-08-10

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US12/310,084 A-371-Of-International US7758659B2 (en) 2006-08-10 2007-07-30 Catalyzed air oxidation haircolor
US12/658,457 Continuation-In-Part US7947090B2 (en) 2006-08-10 2010-02-04 Catalyzed air oxidation haircolor

Publications (2)

Publication Number Publication Date
WO2008020983A2 true WO2008020983A2 (fr) 2008-02-21
WO2008020983A3 WO2008020983A3 (fr) 2008-08-07

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2007/016980 Ceased WO2008020983A2 (fr) 2006-08-10 2007-07-30 Colorant capillaire d'oxydation par l'air catalysée

Country Status (14)

Country Link
US (1) US7758659B2 (fr)
EP (1) EP2059306B1 (fr)
JP (1) JP5339374B2 (fr)
CN (1) CN101528310B (fr)
AR (1) AR062285A1 (fr)
AU (1) AU2007284979B2 (fr)
BR (1) BRPI0716024B1 (fr)
CA (1) CA2659998C (fr)
CL (1) CL2007002305A1 (fr)
ES (1) ES2537083T3 (fr)
MX (1) MX2009001485A (fr)
NZ (1) NZ574744A (fr)
TW (1) TWI409085B (fr)
WO (1) WO2008020983A2 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102470080A (zh) * 2009-07-02 2012-05-23 利兹大学 经催化的染料系统
ITMI20131900A1 (it) * 2013-11-15 2015-05-16 Antonio Arcelli Additivo per tintura per capelli
US10022312B2 (en) 2014-01-24 2018-07-17 Combe Incorporated Gradual haircolor compositions and methods of using the same

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JPH0793128B2 (ja) 1987-03-27 1995-10-09 松下電器産業株式会社 密閉形電池
US7947090B2 (en) * 2006-08-10 2011-05-24 Combe Incorporated Catalyzed air oxidation haircolor
WO2012084568A1 (fr) * 2010-12-20 2012-06-28 Unilever Plc Procédé de coloration de fibres capillaires
CN104257526A (zh) * 2014-10-14 2015-01-07 范黎明 单剂式空气氧化染发剂组合物及其应用
US10245221B2 (en) 2015-05-07 2019-04-02 Celeb LLC Stabilized color depositing shampoo
US9889080B2 (en) 2015-05-07 2018-02-13 Celeb LLC Color depositing shampoo
CN113398007A (zh) * 2021-06-17 2021-09-17 广州潮丽生物科技有限公司 一种单剂型空气氧化的染发剂和制备方法及染发方法
PH12021552091A1 (en) * 2021-07-08 2023-03-27 Korea Advanced Inst Sci & Tech A composition for developing hair color comprising polyphenol
CN116763672A (zh) * 2022-05-13 2023-09-19 佛山市喜妆化妆品有限公司 一种空气氧化的单剂染发产品的制备配方和方法

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HK1128897A1 (en) 2009-11-13
US20090320215A1 (en) 2009-12-31
US7758659B2 (en) 2010-07-20
CN101528310A (zh) 2009-09-09
CN101528310B (zh) 2013-07-17
CA2659998A1 (fr) 2008-02-21
EP2059306A2 (fr) 2009-05-20
MX2009001485A (es) 2009-02-18
AR062285A1 (es) 2008-10-29
WO2008020983A3 (fr) 2008-08-07
ES2537083T3 (es) 2015-06-02
BRPI0716024A2 (pt) 2013-10-08
TWI409085B (zh) 2013-09-21
BRPI0716024B1 (pt) 2015-12-22
NZ574744A (en) 2011-12-22
JP5339374B2 (ja) 2013-11-13
CL2007002305A1 (es) 2008-02-22
EP2059306B1 (fr) 2015-02-18
AU2007284979B2 (en) 2013-03-14
CA2659998C (fr) 2013-10-01
JP2010500349A (ja) 2010-01-07
AU2007284979A1 (en) 2008-02-21
EP2059306A4 (fr) 2012-12-12

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